Trisazo dyestuffs



Patented July 8, 1941 TRISAZO DYESTUFFS Eugen Glietenberg, Leverkusen-I. G.-Werk, and

Josef Hilger and Willi Hartmann, Leverkusen- Wiesdorf;

Germany,

assignors to General Aniline & Film Corporation, a corporation of Delaware No Drawing. Application April 22, 1939, Serial No. 269,410. In Germany May 2, 1938 4 Claims.

The present invention relates to new valuable trisazodyestuffs and to a method of preparing the same; more particularly it relates to trisazodyestuffs of the general formula 3.6- or 4.6-disulfonic acid, then combining in 25 alkaline medium the diazoazo compound obtained with one molecular proportion of a monodiazo compound and thereupon with a derivative of 3-amino-diphenylamine in which one hydrogen atom of the amino group is replaced 30 OH NH:

by an a1kylsu1fo-, arylsulfo or aralkylsulfo radiacids and in general by the property to dye mixed fabrics consisting of various fibres such as cotton, Wool, cellulosic wool, silk, artificial silk uniform and level shades. Compared with the dyestuffs of U. S. Patent 2,012,387 the new dyestuiis show the advantage of an improved fastness to water.

The following examples illustrate our invention Without, however, restricting it thereto, the parts being by weight. v

Example 1 184 parts of i.4-diaminodipheny1 are tetrazotized in the usual manner and coupled with 341 parts of l-amino-Bhydroxynaphthalene-3.6-disulfonic acid in mineral acid medium. This intermediate is combined with a diazo compound prepared from 209 parts of sulfanilic acid (2H2O in a solution alkaline with sodium carbonate. If free diazo compound can no longer be detected a solution of 262 parts of 3-methyl-sulfaminodiphenylamine alkaline with sodium hydroxide is added. After several hours the dyestuff-formation is completed. By adding sodium chloride and neutralizing with mineral acid the dyestuff is separated. It corresponds in its free state to the followingformula:

and dyes leather full bloomy black shades of excellent stability to acids.

If instead of l-amino-8-hydroxynaphthalene- 3.6-disulfonic acid the l-amino-B-hydroxynaphthalene-4.6-disulfonic acid or a mixture of these two acids is used dyestuffs of similar properties but somewhat bluer shades are obtained.

Example 2 184 parts of 4.4'-diaminodiphenyl are tetrazotized in the usual manner and coupled with 341 parts of 1-amino-8-hydroxynaphthalene-3.6-disulfonic acid in mineral acid medium. This intermediate is combined with a diazobenzene solution prepared from 93 parts of aniline, in sodium Example 4 carbonate alkaline medium. If free diazo compound can no longer be detected a solution of 324 If in EXample 2 t benzenesulfaminodiphenparts of 3-benzene-su1faminodiphenylamine alylamine is replaced y Y a kaline with sodium hydroxide is added. After a methyl-1.1-diphenylamine a dyestuff of similar short time the coupling is completed. The dyeproperties is obtained.

stuff is separated in the usual manner. It corresponds in its free state to the following formula:

OH IITHa H V N=N N=N--C N=NNH.SO2.Q0H5

Hoa's- SOaH e 1 111 and dyes cotton'from neutral or sodium carbonate We claim: 3 V V a l alkaline bath green black shades of good fastness 1. As new products trisazody-estufi of t gento water. It possesses the remarkable property r f r i ties is obtained.

to dye *mixed fabrics of various fibres uniform wherein A N N stands for theradica liof a hade w r V monodiazo compoundrof the benzene series, R' If instead of 3 benzenesulfaininodiphenyl stands for a'member selected from the gfoup' amine substitution products thereof are used consisting of alkyl,.ary1. and aralkyl, one X V such'as' 3-(3-chlorobenzenesulfamino)-diphen+ Stands r y ge the. other Xstands for ylamine very similar dyestuffs are obtained. and Y n s for One i v p. 0011- -r g V I sisting of hydrogen, halogen and alkyl. H f

Example 3 I 2. As new products trisazodyestuffs' of the gen- If in Example 2 the '3-benzenesulfaminodieral formula l 7 OH NH:

A X i M o r v V phenylamine is replaced by 3-methylsulfaminowherein AN=N- stands for the radical of a diphenylamine a dyestufi is obtained which monodiazo compound of the benzene series, one shows a somewhat increased solubility. If in- X stands for hydrogen, the other X stands for stead of the 3-methylsulfaminodiphenylamine SO3H, and Y stands for one of the group conthe 3-benzylsulfaminodiphenylamine' is employed sisting of hydrogen, halogen and alkyl.

a dyestuff of similar shade and similar proper- 3; As new product thetrisazodyestuff; corree V spending in its free state to the following formula it v OH NH:

' 'H B NH 7 1 dyeing cotton from neutral bath or bath alkaline with sodium carbonate greenish black shades of good fastness to water.

4. As new product the trisazodyestuff corresponding in its free state to the following formula,

OH NH:

dyeing leather full bloomy black shades of exceilent fastness to acid.

EUGEN G'IIIEX'IENBERG. JOSEF HILGER. WILLI HARTMANN. 

